1,5-Dibromopentane → HCID 20255654, compound

HRID 637694Notes

Reaction equation

HRID 637694 reaction equation
[NH2:1][C:2]1[C:11]([CH3:12])=[CH:10][C:5]2[C:6]([CH3:9])=[CH:7][O:8][C:4]=2[CH:3]=1.Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.C(N(C(C)C)C(C)C)C>C(O)C>[CH3:9][C:6]1[C:5]2[CH:10]=[C:11]([CH3:12])[C:2]([N:1]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)=[CH:3][C:4]=2[O:8][CH:7]=1

Participants

5

Reactant 3

HCID 81001,5-DibromopentaneHCID 81531DiisopropylethylamineHCID 20255642HCID 20255642, compound

Product 1

HCID 20255654HCID 20255654, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 8 g (49.6 mmole) of 6-amino-3,5-dimethylbenzofuran, 23 g (0.1 mole) of 1,5-dibromopentane, 12.9 g (0.1 mole) of N-ethyldiisopropylamine and 60 ml of ethanol is boiled under reflux for 18 hours. The residue obtained after concentration by evaporation in vacuo is taken up in methylene chloride and washed twice with dilute sodium bicarbonate solution. The organic phase is dried, concentrated by evaporation and the crude product is chromatographed with petroleum ether/methylene chloride over silica gel. Distillation of the pure fractions in a bulb tube (130°/10-1 torr) yields 3,5-dimethyl-6-piperidinobenzofuran having a melting point of 64°-66°.

Workup

  1. temperatureunder reflux for 18 hours
  2. customThe residue obtained
  3. concentrationafter concentration
  4. customby evaporation in vacuo
  5. washwashed twice with dilute sodium bicarbonate solution
  6. customThe organic phase is dried
  7. concentrationconcentrated by evaporation
  8. customthe crude product is chromatographed with petroleum ether/methylene chloride over silica gel
  9. distillationDistillation of the pure fractions in a bulb tube (130°/10-1 torr)

Sources & evidence

ORD record
ord-1542bda883b74875abe7640ef616014e
Source dataset
uspto-grants-1985_12
Patent number
US04558043

Reaction notes

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